3,4-dibenzyloxy-6'-hydroxy-2',4'-bis(2-methylbenzyloxy)-3'-(2,3,4,6-tetra-O-benzyl-β-D-glucopyranosyl)chalcone | 321133-85-1

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 直链 1,3-二芳基丙烷
• 英文名称: 3,4-dibenzyloxy-6'-hydroxy-2',4'-bis(2-methylbenzyloxy)-3'-(2,3,4,6-tetra-O-benzyl-β-D-glucopyranosyl)chalcone
• 英文别名: (E)-3-[3,4-bis(phenylmethoxy)phenyl]-1-[6-hydroxy-2,4-bis[(2-methylphenyl)methoxy]-3-[(2S,3S,4R,5R,6R)-3,4,5-tris(phenylmethoxy)-6-(phenylmethoxymethyl)oxan-2-yl]phenyl]prop-2-en-1-one
• CAS: 321133-85-1
• 化学式: C₇₉H₇₄O₁₁
• 分子量: 1199.45
• InChiKey: MZOLNWGSEZJEDM-MYXZHPTCSA-N

物化性质

• 密度：
  1.27±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  15.6
• 重原子数：
  90
• 可旋转键数：
  29
• 环数：
  11.0
• sp3杂化的碳原子比例：
  0.2
• 拓扑面积：
  120
• 氢给体数：
  1
• 氢受体数：
  11

反应信息

• 作为反应物：
  描述：

  3,4-dibenzyloxy-6'-hydroxy-2',4'-bis(2-methylbenzyloxy)-3'-(2,3,4,6-tetra-O-benzyl-β-D-glucopyranosyl)chalcone 在 碘 作用下， 以 二甲基亚砜 为溶剂， 反应 0.25h， 以76%的产率得到2-(3,4-bisbenzyloxyphenyl)-5-hydroxy-7-(2-methylbenzyloxy)-6-(2,3,4,6-tetra-O-benzyl-β-D-glucopyranosyl)-4H-1-benzopyran-4-one
  参考文献：
  名称：

  An effective synthesis of isoorientin: the regioselective synthesis of a 6-C-glucosylflavone

  摘要：

  Isoorientin, a 6-C-beta -D-glucopyranosyl-3',4',5,7-tetrahydroxyflavone, was synthesized in a 15% overall yield, in ten steps, starting from the commercially available phloroacetophenone. The C-glucosyl phloroacetophenone derivative, a synthetic intermediate that contains a free hydroxyl group that is para to the glucosyl moiety, was obtained by hydrogenolysis by taking advantage of differences in the hydrogenolysis rates between a benzyl protecting group and a 2-methylbenzyl protecting group. Aldol condensation of the C-glucosyl phloroacetophenone derivative with 3,4-bis-benzyloxybenzaldehyde afforded the corresponding chalcone as a precursor of the 6-C-glucosyl flavone. Construction of the flavone system by application of I-2-DMSO, followed by deprotection, yielded isoorientin. (C) 2000 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0008-6215(00)00226-3
• 作为产物：
  描述：

  1-(2-(benzyloxy)-4,6-dihydroxyphenyl)ethan-1-one 在 palladium on activated charcoal sodium hydroxide 、 4 A molecular sieve 、 三氟化硼乙醚 、 氢气 、 potassium carbonate 作用下， 以 1,4-二氧六环 、 二氯甲烷 、 水 、 乙酸乙酯 、 N,N-二甲基甲酰胺 为溶剂， 反应 29.0h， 生成 3,4-dibenzyloxy-6'-hydroxy-2',4'-bis(2-methylbenzyloxy)-3'-(2,3,4,6-tetra-O-benzyl-β-D-glucopyranosyl)chalcone
  参考文献：
  名称：

  An effective synthesis of isoorientin: the regioselective synthesis of a 6-C-glucosylflavone

  摘要：

  Isoorientin, a 6-C-beta -D-glucopyranosyl-3',4',5,7-tetrahydroxyflavone, was synthesized in a 15% overall yield, in ten steps, starting from the commercially available phloroacetophenone. The C-glucosyl phloroacetophenone derivative, a synthetic intermediate that contains a free hydroxyl group that is para to the glucosyl moiety, was obtained by hydrogenolysis by taking advantage of differences in the hydrogenolysis rates between a benzyl protecting group and a 2-methylbenzyl protecting group. Aldol condensation of the C-glucosyl phloroacetophenone derivative with 3,4-bis-benzyloxybenzaldehyde afforded the corresponding chalcone as a precursor of the 6-C-glucosyl flavone. Construction of the flavone system by application of I-2-DMSO, followed by deprotection, yielded isoorientin. (C) 2000 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0008-6215(00)00226-3